Organic Chemistry A Short Course 13th Edition By Harold Hart – Test Bank

6. Which of the following molecules has the highest boiling point?
A) ethylamine
B) propane
C) ethyl alcohol
D) dimethyl ether
E) acetaldehyde

ANS: C TOP: Properties of Amines

7. To separate a mixture of p-toluidine and p-nitrotoluene dissolved in ether,
A) extract the ether solution with aqueous HCl and treat the water layer with aqueous NaOH.
B) extract the ether solution with aqueous NaOH and treat the water layer with aqueous HCl.
C) extract the ether solution with water and treat the water layer with aqueous NaOH.
D) extract the ether layer with aqueous HCl and treat the ether layer with aqueous NaOH.
E) extract the ether solution with aqueous HCl and treat the ether layer with aqueous HCl.

ANS: A TOP: Properties of Amines

8. Which of the following statements is false:
A) Aliphatic 3o amines with three different groups on nitrogen can be resolved.
B) Primary and secondary aliphatic amines can be hydrogen bond donors.
C) Aliphatic amines can be hydrogen bond acceptors.
D) The non-bonded lone pair in an aliphatic amine is more basic than the non-bonded lone pairs in ethers.
E) The nitrogen in aliphatic amines is sp3-hybridized.

ANS: A TOP: Properties of Amines

9. Which compound is the strongest base?
A) CH3NH2
B) CH3CO2H
C) CH3CHO
D) CH3OH
E) C6H5NH2

ANS: A TOP: Acid-Base Chemistry

10. Which of the following amines is the most basic?
A) methylamine
B) dimethylamine
C) ammonia
D) aniline
E) N-methylaniline

ANS: B TOP: Acid-Base Chemistry

14. When methylamine (CH3NH2) reacts with methyl bromide (CH3Br) to give dimethylamine, the methylamine:
A) acts as an electrophile
B) acts as a Lewis acid
C) acts as a Bronsted-Lowry acid
D) acts as a Bronsted-Lowry base
E) acts as a nucleophile in an SN2 reaction

ANS: E TOP: Reaction Mechanisms

16. The mechanism by which acylation of an amine with an acid chloride takes place is:
A) nucleophilic acyl substitution
B) electrophilic aromatic substitution
C) nucleophilic addition
D) electrophilic addition
E) nucleophilic aromatic substitution

ANS: A TOP: Reaction Mechanisms

17. The alkylation of an amine with an alkyl halide takes place by the following mechanism:
A) SN1
B) SN2
C) electrophilic addition
D) E1
E) E2

ANS: B TOP: Reaction Mechanisms

21. Reacting aniline, C6H5NH2, with a primary alkyl halide will produce a(n):
A) 1° amine
B) 2° amine
C) 3° amine
D) amide
E) imine

ANS: B TOP: Reactions

22. An imine is produced when a ketone or aldehyde reacts with:
A) methyl alcohol
B) Zn(Hg), HCl
C) an amine
D) an amide
E) HCN

ANS: C TOP: Reactions

24. What is the stereochemical relationship of the products formed by reacting racemic lactic acid with (S)-1-phenylethylamine?
A) enantiomers
B) meso compounds
C) racemic mixture
D) diastereomers
E) geometric isomers

ANS: D TOP: Reactions